2-(DiMethylphosphoryl)benzenamine

Name: 2-(DiMethylphosphoryl)benzenamine
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CAS No. 1197953-47-1
Cat. No. CS-W005746
Purity≥98%
MDL No.MFCD23135529

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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2-(DiMethylphosphoryl)benzenamine|CS-W005746

Structure of 1197953-47-1

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General Information

CAS No. 1197953-47-1
Cat. No. CS-W005746
Purity ≥98%
MDL No. MFCD23135529
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₁₂NOP
Molecular Weight 169.16
Synonym(s) None
SMILES CP(C)(=O)C1=C(N)C=CC=C1

Description

(2-Aminophenyl)dimethylphosphine oxide features a phosphine oxide moiety tethered to an ortho-aminophenyl group, delivering a sterically accessible coordination site. This bench-stable ligand integrates readily into palladium-catalyzed cross-coupling systems, enabling efficient bond formation under mild conditions.

Application

(2-Aminophenyl)dimethylphosphine oxide serves as a versatile ligand in transition metal catalysis, particularly in palladium-catalyzed cross-coupling reactions. Its ortho-amino group enables chelation to metals, enhancing catalyst stability and reactivity. The dimethylphosphine oxide moiety offers good bench stability, mild handling, and tolerance to various functional groups, facilitating efficient synthesis of biaryl and heterocyclic scaffolds common in medicinal chemistry.

Synthesis

Route1
- In-stock
  
  615-43-0
- 7211-39-4
- ~77%
- In-stock
  
  1197953-47-1
References
- ARIAD PHARMACEUTICALS, INC.; ZHU, Xiaotian; WANG, Yihan; SHAKESPEARE, William, C.; HUANG, Wei-Sheng; DALGARNO, David, C. Patent: WO2013/169401 A1, 2013 ; Location in patent: Page/Page column 41-42 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 43.09
LogP 1.5168
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-(DiMethylphosphoryl)benzenamine

CAS No. 1197953-47-1

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